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472654

Sigma-Aldrich

N-Boc-2-aminoacetaldehyde

95%

Synonym(s):

tert-Butyl N-(2-oxoethyl)carbamate

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About This Item

Linear Formula:
HCOCH2NHCO2C(CH3)3
CAS Number:
89711-08-0
Molecular Weight:
159.18
MDL number:
MFCD01321273
UNSPSC Code:
12352100
PubChem Substance ID:
24870815
NACRES:
NA.22

Quality Level

100

assay

95%

refractive index

n20/D 1.455 (lit.)

storage temp.

−20°C

SMILES string

CC(C)(C)OC(=O)NCC=O

InChI

1S/C7H13NO3/c1-7(2,3)11-6(10)8-4-5-9/h5H,4H2,1-3H3,(H,8,10)

InChI key

ACNRTYKOPZDRCO-UHFFFAOYSA-N

Gene Information

human ... CTSK(1513)

Related Categories

General description

N-Boc-2-aminoacetaldehyde is an organic building block. It reacts with Horner-Wadsworth-Emmons (HWE) reagent to afford γ-aminobutyric acid (GABA)-derived α-keto amide/ester units.

Application

α-Methylenation of this amino aldehyde proceeds in a quick and efficient manner using a recently reported protocol involving formaldehyde and catalysis by either pyrrolidine proprionic acid or the dipeptide L-Pro-β-Ala.
Also used in a three-component synthesis of pyrrolidines involving 1,3-dipolar cycloaddition.
N-Boc-2-aminoacetaldehyde may be employed in the following:
  • As a starting reagent in the total synthesis of (+)-negamycin.
  • Synthesis of (E)-ethyl 4-((tert-butoxycarbonyl)amino)but-2-enoate.
  • Synthesis of 2,2′-bipyridine.
A building block in the synthesis of a protected pyrroloproline.

wgk_germany

WGK 3

flash_point_f

closed cup

flash_point_c

closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anniina Erkkilä et al.
The Journal of organic chemistry, 71(6), 2538-2541 (2006-03-11)
A rapid and extremely convenient method for alpha-methylenation of aldehydes with aqueous formaldehyde is described. Two optimal catalytic systems are presented that allow short reaction times and afford the functionalized products in good to excellent yields (up to 99%) and
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